Terbinafine

Modify Date: 2024-01-02 12:11:08

Terbinafine Structure
Terbinafine structure
 Common Name Terbinafine
CAS Number 91161-71-6 Molecular Weight 291.430
Density 1.0±0.1 g/cm3 Boiling Point 417.9±33.0 °C at 760 mmHg
Molecular Formula C21H25N Melting Point N/A
MSDS N/A Flash Point 183.7±22.3 °C

 Use of Terbinafine


Terbinafine (TDT 067) is an antifungal medication used to treat fungal infections. It is a potent non-competitive inhibitor of squalene epoxidase from Candida with a Ki of 30 nM.

 Names

Name terbinafine
Synonym More Synonyms

 Terbinafine Biological Activity

Description Terbinafine (TDT 067) is an antifungal medication used to treat fungal infections. It is a potent non-competitive inhibitor of squalene epoxidase from Candida with a Ki of 30 nM.
Related Catalog
Target

Ki: 30 nM (squalene epoxidase)[1]

In Vitro Terbinafine has a primary fungicidal action in vitro against most fungal pathogens, including dermatophytes, and dimorphic and filamentous fungi. Terbinafine specifically inhibits fungal ergosterol biosynthesis at the point of squalene epoxidation. The treated fungal cells rapidly accumulate tlic intermediate squalene and become deficient in the end-product of the pathway, ergosterol[1].
In Vivo Terbinafine is not only active after topical application but is very effective in experimental dermatophytoses following oral administration. In fungi infected guinea-pigs, the skin temperature dropps dramatically after the fourth treatment of terbinafine[2].
Animal Admin Guinea-pigs: The backs (lumbar regions) of guinea-pigs, which have been mechanically depilated, are infected with 0.1 mL Sabouraud's dextrose 2% broth containing 106 c.f.u. of Truhophyton mentagrophytes. The treatments commence 48 h post-inoculation. The test compounds (Terbinafine) are suspended in 2% tylose and Tween 80 and administered via a stomach tube once daily on 9 consecutive days, or dissolved in a mixture of polyethylene glycol 400 and etbanol and spread on the infected part ot the body in a volume of 0.4 mL with a Hrigalski spatula once daily for 1-7 consecutive days[2].
References

[1]. Ryder NS, et al. Terbinafine: mode of action and properties of the squalene epoxidase inhibition. Br J Dermatol. 1992 Feb;126 Suppl 39:2-7.

[2]. Mieth H, et al. Preclinical evaluation of terbinafine in vivo. Clin Exp Dermatol. 1989 Mar;14(2):104-7.

 Chemical & Physical Properties

Density 1.0±0.1 g/cm3
Boiling Point 417.9±33.0 °C at 760 mmHg
Molecular Formula C21H25N
Molecular Weight 291.430
Flash Point 183.7±22.3 °C
Exact Mass 291.198700
PSA 3.24000
LogP 6.61
Vapour Pressure 0.0±1.0 mmHg at 25°C
Index of Refraction 1.586

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QJ8600000
CHEMICAL NAME :
1-Naphthalenemethanamine, N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-, (E)-
CAS REGISTRY NUMBER :
91161-71-6
LAST UPDATED :
199709
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C21-H25-N
MOLECULAR WEIGHT :
291.47

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
210 mg/kg/6W-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Taste) - change in function
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 340,728,1992
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
3918 ug/kg
TOXIC EFFECTS :
Gastrointestinal - other changes
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 27,6087,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
200 mg/kg/40D-I
TOXIC EFFECTS :
Behavioral - anorexia (human) Liver - jaundice, cholestatic Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
JOHEEC Journal of Hepathology. (Elsevier Science, 655 Avenue of the Americas, New York, NY 10010) V.1- 1985- Volume(issue)/page/year: 24,753,1996
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 9,427,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
213 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
53XPA8 "Proceedings of the International Congress of Chemotherapy, 13th, Vienna, 1983," Spitzy, K.H., and K. Karrer, eds., 18 vols., Vienna, Austria, Verlag H. Egermann, 1983 Volume(issue)/page/year: 6,116/52,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 9,427,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
393 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
53XPA8 "Proceedings of the International Congress of Chemotherapy, 13th, Vienna, 1983," Spitzy, K.H., and K. Karrer, eds., 18 vols., Vienna, Austria, Verlag H. Egermann, 1983 Volume(issue)/page/year: 6,116/52,1983

 Safety Information

Hazard Codes Xi
Risk Phrases 36/37/38
Safety Phrases S26-S36/37/39
HS Code 2921499090

 Synthetic Route

 Customs

HS Code 2921499090
Summary 2921499090 other aromatic monoamines and their derivatives; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

 Synonyms

Lamasil
UNII-G7RIW8S0XP
1-naphthalenemethanamine, N-[(2E)-6,6-dimethyl-2-hepten-4-ynyl]-N-methyl-
1-Naphthalenemethanamine, N-[(2E)-6,6-dimethyl-2-hepten-4-yn-1-yl]-N-methyl-
S1725_Selleck
Terbinafine
Lamisil AT
trans-N-Methyl-N-(1-naphthylmethyl)-6,6-dimethylhept-2-en-4-ynyl-1-amine
(E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine
Lamisil
Lamasil (TN)
(2E)-N,6,6-Trimethyl-N-(1-naphthylmethyl)hept-2-en-4-yn-1-amine
(2E)-N,6,6-Trimethyl-N-(1-naphthylmethyl)-2-hepten-4-yn-1-amine
SF-86-327
EINECS 245-385-8
MFCD00242672
Lamisil Tablet
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